Khan Shaykhun is located at an altitude of 350 meters on the main highway between Aleppo and Damascus. The local economy is primarily agricultural, focusing on the growing of cotton and cereals.[2] The town was formerly known for producing embroidery.[3] Nearby localities include Hbit to the west, Kafr Zita to southwest, Murak to the south and Al-Tamanah to the east. In 2004, it was recorded as having 34,371 inhabitants.[4]

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Khan Shaykhun takes its name from a 14th-century khan or caravanserai built by the Mamlukemir Sayf al-Din Shaykhu al-'Umari.[5][6] The town grew up around the khan and is situated below a prominent tell, where excavations carried out in 1930 under the French Comte du Mesnil du Buisson revealed evidence of habitation dating back to the 20th century BC.[2][7] The tell, which measures about 200–250 m long by 18–24 m high, was levelled off in the Bronze and Iron Ages to provide a platform for a series of walled towns built successively on top of each other. The second of these, dating to about 700 BC, has been identified as the Assyrian town of Ashkhani. The site was abandoned around 300 BC.[8]

In more recent times, Khan Shaykhun was noted for its beehive houses, an architectural style found across the Levant and probably exported from there to North Africa.[9] It was described in 1902 by the traveller Henry James Ross as "a miserable looking village"[10] and remained small until relatively recently. In 1966 it was recorded as having only around 3,000 inhabitants.[6]

On 4 April 2017, the town came under a heavy air attack, using chemical weapons.[12] 86 people were killed.[13][14][15][16] After a few months of relative calm, the town was bombed again in September 2017.[17] Jets believed to be Russian destroyed the town’s power plant, which feeds northern Hama and southern Idlib.[18] The al-Rahma clinic was also struck.[19]

On 27 February 2018, pro-government media reported that HTS withdrew from the city of Khan Shaykhun, and was expelled from western Aleppo.[20] In mid-April 2018, pro-opposition media reported that HTS once again seized the town, which had been devoid of rebel military presence.[21] In August 2018, the town again came under aerial bombardment by pro-government forces.[22][23]